Thiourea → Methyl1-[4-(2-amino-1,3-thiazol-4-yl)phenyl]cyclopropanecarboxylate

HRID 969109Notes

Reaction equation

HRID 969109 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2([C:14]([O:16][CH3:17])=[O:15])[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)=O.[NH2:18][C:19]([NH2:21])=[S:20]>C(O)C.C(OCC)(=O)C>[NH2:21][C:19]1[S:20][CH:2]=[C:3]([C:5]2[CH:10]=[CH:9][C:8]([C:11]3([C:14]([O:16][CH3:17])=[O:15])[CH2:13][CH2:12]3)=[CH:7][CH:6]=2)[N:18]=1

Participants

5

Reactant 2

HCID 2723790ThioureaHCID 86602275Methyl1-[4-(chloroacetyl)phenyl]cyclopropanecarboxylate

Product 1

HCID 86602276Methyl1-[4-(2-amino-1,3-thiazol-4-yl)phenyl]cyclopropanecarboxylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 1-[4-(chloroacetyl)phenyl]cyclopropanecarboxylate (0.30 g, 1.2 mmol) and thiourea (0.18 g, 2.4 mmol) in ethanol (5.0 ml) was refluxed overnight. The reaction mixture was diluted with ethyl acetate and washed with saturated NaHCO3 and brinesuccessively; then dried; and then concentrated. The residue was tritrurated with ether followed by filtration to afford the product. LC-MS: 275.1 (M+H)+.

Workup

  1. temperaturewas refluxed overnight
  2. washwashed with saturated NaHCO3
  3. customthen dried
  4. concentrationand then concentrated
  5. filtrationfollowed by filtration
  6. customto afford the product

Sources & evidence

ORD record
ord-303045192b254de981f9fedc40790140
Source dataset
uspto-grants-2007_12
Patent number
US07304081B2

Reaction notes

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